The Price of Free Speech, Part 3

The day after my first spanking was very “interesting” to say the least. I could not sit without feeling a tinge of pain in my ass and thighs. Whenever I thought of the events of the previous day, I got turned on. Remembering the embarrassment of having to strip in front of a stranger and take a beating that could break anyone was so intense. Aside from the little finger incident, I so badly wanted to experience it all again.

I returned to Miss Jones for three more sessions of spanking and humiliation as ordered. The first maintenance spanking was fairly easy. She had me pose bent over in those pink nylon panties as she hand spanked me, then pulled them down for about a dozen stinging swats with her yard stick. As promised, she had a new pair of women’s panties for me to wear, this time white cotton. I could not figure it out, but she got really into things when she had me wear her underwear. Never before had I met a woman that got all hot from seeing a man in women’s underwear. Truthfully, I was freaked out by having to wear them the first time, but then figured that it was no big deal since I only saw them when I put them on in the morning, and she saw them when I striped for her. What was her fetish with the panties?

The second session seemed more like a traditional school scene spanking. You know, like something you would see in a porno movie. Miss Jones bent me over the desk bare assed and took her riding crop to me until I whimpered from the pain. She would not try to bring me to tears. Ever time she sensed my limits were being pushed, she held back then told me what a good boy I was. Thirty-five spanks on my bare ass were endured. That night it was really hard to sit again.

Our third meeting got creative. Miss Jones took the leather belt from my pants and spanked me while wearing her underwear for over a half hour. I could not count the spanks. All I knew was that I really regretted opening my mouth four days earlier, and that tomorrow could not come fast enough. You see tomorrow was Saturday, which would be the last of our meetings. My mind was definitely made up. After Saturday never again would I let a woman spank me for any reason. I was going to be a top only, and totally throw out the switch attitude that I had.

So here we are at Saturday, my last spanking session. Finally, no more panties to wear, no more stings to endure. The day went by just like any other day, and then it was time for my “meeting”. I knocked on her classroom door, and was invited in. Miss Jones stood there behind her desk, arms crossed and looking just as stern as ever. “Mr. Bryan, seems that I had you all wrong. You are more of a man then I thought you were. I never expected you to actually make it through the week.” Wow! I was surprised. This was the first time ever that I heard this woman pay me a complement and not mean it sarcastically. “Well Mr. Bryan, now it is time for me to fully explain myself to you, and why I had you endure such a punishment. First, please remove you pants so that I can make sure you have panties on, and take a seat in my chair”.

Regardless of how the week had gone, I still felt strange about wearing a pair of panties, and having to sit with them in front of this woman. It would have been easier for me to stand bare assed then for me to wear these stinking panties. Of course, I did as Miss Jones said, and sat in her chair waiting for her explanation.

“As a young girl, Mr. Bryan, I was forced to take extreme punishments from my mother and father for whatever infraction it was that I committed. Imagine being spanked in front of a room full of your parents friends for coming home 2 minutes late on a Friday night, or having your face washed in front of your friends before going out to make sure you did not have on any make up. You see, this is what molded me into what I am.” Miss Jones circled me, and unbuttoned her shirt exposing a firm set of beautiful tits encased in a lacy white bra. She then reached into her purse and put a small vibrator on the desk in front of me. “Mr. Bryan, what I am about to tell you will stay between us, or you know what will happen. I have never had sex with a man before. I do have a girlfriend, and we explore our sexuality orally and with toys like this vibrator together. Yes, I am a lesbian, and proud of the fact, but do not openly advertise it out of fear of being shunned by the parents of my students. Tonight’s session is not about punishment, but about sexual education… sexual education that you are going to teach me.”

My Lord! I was totally speechless. Here I am thinking that I am going to get the shit beat out of me for a fourth day in a row, but instead I’m going to fuck the bejezus out of this woman! “Mr. Bryan, I liked seeing you in my panties because it is nothing more than a pure turn on to me. I knew it would humiliate you, and that was part of the purpose too. It’s just that I kept getting turned on more and more, so I kept having you wear them.” It was all coming full circle. Miss Jones likes women, so seeing me in a woman’s pair of underwear became an unexpected turn on. “Mr. Bryan, to truly be an effective top, you must first endure much as a bottom. You have endured what I feel is acceptable. I want you to spank me, as I have spanked you. Long, hard, and vicious. I also want you to take advantage of me in any way you want. Do as you please with me, just as long as you spank and fuck me. Yes, I want you to be the first man in this 35 year old virgin pussy other than my “plastic” man.”

Immediately, I took her by the arm and threw her across my lap. I pulled up her skirt and slid her silky blue panties down to her knees. My fingers slipped in and out of her hot swollen mound, making it wetter and wetter. I paused, and then spanked her long and hard with my bare hand. She was breathing heavy, and I could see her inner thighs becoming wet from her dripping pussy. SPANK, SPANK, SPANK, SPANK, about 50 swats to her hot ass. I stood her up and put her in the corner. “Well well Miss Jones, who is naughty now? I think you need to have a taste of your own medicine. Strip down out of all your clothes, bra, stocking, panties, all of it, and walk over to the chalkboard. Put your hands on that chalkboard and lean forward.”

I looked over into the chalkboard ledge and saw a long, thin, wooden pointer stick. A devious smile came across my face as I picked it up. Rubbing it gently across her firm, rosy red ass, I told her that she needed a reminder on proper classroom etiquette. “Miss Jones, I do respect your admiration for strict discipline, but you do need to be reminded that other people have different opinions, and you should respect what they have to say.” WHACK, WHACK, WHACK! I landed three, hard fast swats onto her ass. She instantly cried out and burst into tears. Her skin blistered up and turned a dark shade of red. WHACK, WHACK, WHACK, WHACK! I continued and gave her 10 more slowly paced shots, blistering her whole ass almost to the point of bleeding.

Miss Jones was crying like a baby. She was constantly apologizing for her ignorant attitude, and begging for forgiveness. After admiring my handy work for a minute, I spun her around and kissed her hard, grabbing her painful ass and rubbing her tits. She let out a moan of ecstasy. Next, I bent her over the closest desk, and spread her legs apart. I ripped off those stinking panties that she had me wear to release my rock hard cock.

“Now Miss Jones, you can have your pleasure”. I took my member and shoved it hard into her soaking wet pussy, thrusting hard and fast, making sure that my pelvis contacted her blistered ass with every stroke. In and out, in and out, I fucked her furiously for about 20 minutes. When it was time for me to cum, I pulled it out and forced her mouth onto my cock, making sure that she swallowed every drop of my explosion, not letting out a single drop.

When we were finished, Miss Jones put her arms around me, and with the mixed sound of pleasure and pain in her voice, thanked me for spanking her proper, an
d giving her a hard fuck. I held her for a while until she calmed down and gained her composure. We got cleaned up and dressed, then said our goodbye.

That was about a month and a half ago. Since then, Miss Jones always has greeted me with a wink and a smile. I too make sure to wish her a good day, and grant her a pleasant glance. Will Miss Jones ever spank me again? Will I ever have the chance to have my way with such a firm, beautiful ass again? I guess only time will tell!